Asymmetrical nonbridgehead nitrogen-17: Complete separation into antipodes and absolute configuration of chiralic n-alkoxyisoxazolidines |
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| Authors: | Remir G Kostyanovsky Vladimir F Rudchenko Oleg A D&#x;yachenko Ivan I Chervin Aleksandr B Zolotoi Lev O Atovmyan |
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| Institution: | Institute of Chemical Physics, Academy of Sciences of the U.S.S.R. Moscow, U.S.S.R. |
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| Abstract: | trans-Stereospecificity of the amidation of 1-alkoxyisoxazolidine-3,3-dicarboxylic ester (1) has been elucidated. Alkaline hydrolysis of monester 4 yielded the salt 6 which after its ion exchange in the form of S(?) and R-(+)-phenylethylammonium salts was completely separated into the enantiomeric salts (+10 and ?10). Esterification and amidation of these salts afforded antipodes 2 S-( +12) and 2 R-( ?12) containing only a nitrogen asymmetric center. Optical purities of the products were established on the basis of their NMR spectra with shift-reagent. Molecular and crystal structure as well as an absolute configuration of +10 were detected by means of X-ray analysis. |
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